How To Pack for 2 Weeks in a Carry On

Historically, I’ve always been a bit of an over-packer. I like to be prepared for any occasion and I like to have my options! So the idea of packing for a long trip in a carry-on suitcase (I hate checking a bag!) can be a daunting one.

However, I’ve packed for a two-week Hawaii and Las Vegas trip and a two-week European trip in a carry-on suitcase, among many other shorter trips, so I’ve realized this has become something I’ve gotten pretty good at, so i wanted to share my top tip and tricks!

How to Pack for 2 Weeks in a Carry On


1- Make a list. This is probably the first thing I do when I have a trip planned. It doesn’t matter if I’m going away for a weekend or for 2 weeks. If it’s not on the list, it’s not getting packed and I note everything from outfits to underwear to hair products to accessories. (I might depend on lists a little too much…if such a thing is possible.)


2- Roll your clothes. Not only does this allow you to have more space but rolling your clothes actually helps protect them from wrinkles. This is my #1 packing trick! I roll up every article of clothing as small as I possibly can. It’s truly amazing how much you’ll be able to stuff in your bag.


3- Get Creative! Tucked that rolled up underwear into your shoes. Wear your bulkiest sweater and biggest pair of shoes on the plane. See my black bag in the above picture? It’s filled with jewelry and miscellaneous toiletries. Take advantage of all pockets in your suitcase. Any way you can maximize space, do it.

4- Pack Travel Sized Toiletries. I have a rule, if it doesn’t fit in the allotted 3 ounce liquid carry on container, I don’t bring it. I’ll pack travel size toothpaste, face wash, sunblock, hair products, etc. If I run out of something or it doesn’t fit, I’ll buy it at my destination.


5- Pack Multi-Functional Pieces. I’m not always the best at this. I love having my closet at my disposal and like the idea of options depending on the weather or occasion. However, if packing for a long trip I have to be realistic and realize I need to re-wear an outfit or pack pieces that I can use for a top to wear out one day and then transform to a night out the next.

For example, if you’re traveling to a city, take your favorite pair of black pants. These can go from sightseeing during the day with a pair of sneakers or comfortable sandals, and easily transition to night with pair of sleek black heels, a silky top, and a statement necklace.

If you’re traveling to an island or a warmer climate, sundresses are your best friend. You can wear one out for dinner one night with your favorite pair of wedges and jewelry and the next day throw it over your bathing suit as you head to the beach.

Here’s an example of where I recycled the exact same outfit:

Hawaii 1
White tank and purple maxi skirt (with wedges, not pictured) out for dinner in Waikiki Beach, Hawaii.
Las Vegas
Next up, a small airplane tour of the Grand Canyon from the second half of our Hawaiian/Las Vegas adventure.

6- Be Prepared. Just in case your carry on has to get gate checked, make sure you pack an extra pair of underwear, socks, an extra outfit (if it will fit), expensive jewelry, and all necessary medications in your personal bag (such as a purse or backpack) that you will keep with you on your flight.

You’ll want this just in case your checked bag doesn’t make it to your destination at the same time you do. This way, at least you’ll have your necessaries, your valuables, and hopefully a fresh pair of underpants while you bide your time!


And on that note, I’m off to New Orleans today for my 1-year wedding anniversary. I can’t wait to fill you in on all our adventures! 🙂

4 thoughts on “How To Pack for 2 Weeks in a Carry On

  1. Super impressive.

    My goal for my girls trip this summer is a small suitcase. I hope to fly SW so I won’t have to worry about baggage costs but still want one small suitcase…..we will see how it goes!!

    Happy anniversary. ..have fun!!


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